CN110305050A - A kind of method that 5- [2- (methyl mercapto) ethyl] glycolylurea hydrolysis exhaust prepares Sodium L-methioninate - Google Patents
A kind of method that 5- [2- (methyl mercapto) ethyl] glycolylurea hydrolysis exhaust prepares Sodium L-methioninate Download PDFInfo
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- CN110305050A CN110305050A CN201910652656.4A CN201910652656A CN110305050A CN 110305050 A CN110305050 A CN 110305050A CN 201910652656 A CN201910652656 A CN 201910652656A CN 110305050 A CN110305050 A CN 110305050A
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- glycolylurea
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of method that 5- [2- (methyl mercapto) ethyl] glycolylurea hydrolysis exhaust prepares Sodium L-methioninate, comprising: mixes aqueous solution of the glycolylurea aqueous solution with alkali or containing alkali；Resulting mixed liquor is heated to 140 DEG C of -190 DEG C of reactions, is exhausted in reaction process, reaction obtains the saponification liquor containing Sodium L-methioninate.The present invention is vented in 5- [2- (methyl mercapto) ethyl] glycolylurea hydrolytic process, on the one hand the investment of alkali can be reduced, energy consumption can be reduced on the other hand, ion-exchange processing capacity can also greatly be promoted, substantially reduce the by-product of sodium sulphate during producing methionine, and this method is simple, easy to operate, exploitativeness is strong.
Description
Technical field
The present invention relates to chemical fields, further to methionine production technical field, more particularly to a kind of 5- [2-
(methyl mercapto) ethyl] the glycolylurea hydrolysis exhaust method for preparing Sodium L-methioninate.
Background technique
Methionine also known as methionine are the nonpolar alpha amino acids of sulfur-bearing, are one of essential amino acids of human body, extensively
For feed addictive, food additives and pharmaceutical raw material.At present prepare methionine technique mainly include microbe fermentation method,
Biological enzyme disassembles method and chemical synthesis；Biological enzyme disassembles method and microbe fermentation method yield is low, at high cost, does not have also at present
Industrial production value.The main production of methionine is to use to generate using methacrylaldehyde and methyl mercaptan as raw material both at home and abroad at present
Methylthiopropionaldehyde, methylthiopropionaldehyde and Cymag, the ammonia spirit generation condensation reaction of ammonium bicarbonate, basic hydrolysis, acidification production egg ammonia
Acid, hydrolysis is different with acidification route, and the by-product of generation is also different, and existing methionine preparation process mainly uses sodium hydroxide alkali
Hydrolysis generates Sodium L-methioninate, then is acidified finished product methionine, and by-product anhydrous sodium sulfate with sulfuric acid.
Domestic methionine manufacturing enterprise mostly uses greatly above-mentioned production technology, but due to the rise of the methionine prices of raw materials, egg
Separation problem, methionine product purity problem, brine waste emission problem of propylhomoserin and sulfuric acid mother liquid of sodium etc. one is problem, is caused
Methionine product quality is relatively poor, and there are the feature of environmental protection it is poor, at high cost the problems such as.
Chinese patent CN105949097A discloses a kind of use will the aqueous solution containing methionine and methionine glycolylurea water
The method for solving the reaction of liquid Hybrid Heating, the process efficiently solve the exhausting problem of methionine ion-exchange, effectively reduce
Impurity in methionine crystalline mother solution.But methionine glycolylurea hydrolysising alkali, which consumes high problem, not to be well solved, it is main
Have the following problems: (1) methionine glycolylurea hydrolysis will consume a large amount of sodium hydroxide, and total sodium does not subtract in obtained saponification liquor
It is few, it is exchanged in entering ion exchange system by h type resin, resin treatment ability could not be improved.(2) resin after exchanging
A large amount of sodium ions are combined with, H need to be used2SO4Regeneration, it is clear that sulfuric acid consumption is higher, generates more cheap sodium sulphate.
For above-mentioned methionine glycolylurea hydrolysis lead to the problem of more sodium carbonate, alkali consume it is high, because of the generation of sodium carbonate
It is the content height and 5- (2- methylthio ethyl second of the sodium carbonate as caused by methionine production technology itself, in saponification liquor
Base)-hydantoins (glycolylurea) hydrolysis when alkali dosage it is related, the dosage for reducing alkali is can to reduce containing for sodium carbonate in saponification liquor
Amount, but existing technique is pressed, this necessarily causes glycolylurea hydrolysis to be not thorough, so as to cause impurity mistake in methionine crystalline mother solution
It is more, Recycling Mother Solution number reduce the problems such as.
Summary of the invention
In view of the foregoing deficiencies of prior art, the purpose of the present invention is to provide a kind of 5- [2- (methyl mercapto) ethyls]
The glycolylurea hydrolysis exhaust method for preparing Sodium L-methioninate, for solve to remain when in the prior art prepared by methionine a large amount of carbonates,
The problems such as capacity is high when subsequent ion being caused to exchange, by-product a large amount of sodium sulphate.
In order to achieve the above objects and other related objects, the present invention provides a kind of 5- [2- (methyl mercapto) ethyl] glycolylurea hydrolysis
The method that exhaust prepares methionine, comprising: mix aqueous solution of the glycolylurea aqueous solution with alkali or containing alkali；Resulting mixed liquor adds
Heat is exhausted in reaction process to 140 DEG C of -190 DEG C of reactions, obtains the saponification liquor containing Sodium L-methioninate.
Reaction temperature is specifically as follows 140 DEG C, 145 DEG C, 150 DEG C, 155 DEG C, 160 DEG C, 165 DEG C, 170 DEG C, 175 DEG C, 180
DEG C, 185 DEG C, 190 DEG C etc..
Optionally, the reaction is carried out in closed container, pressure >=0.7MPa in the closed container.
Optionally, the pressure in the closed container be 0.7-1.1MPa, be specifically as follows 0.7MPa, 0.8MPa,
0.9MPa, 1.0MPa, 1.1MPa, 1.2MPa, 1.3MPa etc. maintain the pressure in the closed container by exhaust.
Optionally, the content of 5- [2- (methyl mercapto) ethyl] glycolylurea is 10wt%-20wt% in the glycolylurea aqueous solution.
The Chinese of 5- [2- (methyl mercapto) ethyl] glycolylurea further includes 5- [2- (first sulphur) ethyl]-hydantoins, 5- [2-
(first sulphur) ethyl] -2,4- imidazolidimedione, 5- [2- (first sulphur) ethyl] hydantoins, acyl in 5- [2- methyl thio acetyl] second
Deng, CAS 13253-44-6, molecular formula: C6H10N2O2S。
Optionally, the glycolylurea Na in Solution ion concentration is 1.6wt%-2.6wt%, and sodium ions content depends on upper
Trip technique, the resulting glycolylurea aqueous solution of different process all can be used as raw material of the invention, be hydrolyzed using technique of the invention.
For example, resulting glycolylurea aqueous solution sodium ions content is extremely low in other techniques, it is equally applicable to the present invention.
Glycolylurea synthetic method has one-step method, two-step method at present, and the raw material of both methods throws process difference, but produces
Raw glycolylurea sodium content is higher, and sodium ions content theory is zero in the glycolylurea that cyanalcohol method is synthetically produced, and hydrolysis alkali equivalent should be greater than
1, carbonate content is calculated by total sodium.
Optionally, the glycolylurea aqueous solution is the aqueous solution containing 5- [2- (methyl mercapto) ethyl] glycolylurea and sodium carbonate.
Optionally, the molar ratio of the alkali and 5- [2- (methyl mercapto) ethyl] glycolylurea in the glycolylurea aqueous solution is (0.6-
1): 1, it is specifically as follows 0.6: 1,0.7: 1,0.8: 1,0.9: 1,1: 1 etc..
Optionally, the alkali is selected from least one of sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate.
Optionally, the mass fraction of alkali is 40wt%-55wt% in the aqueous solution containing alkali.
Optionally, carbonate content≤1.5wt% in the saponification liquor obtained.
The present invention also provides utilize Sodium L-methioninate made from the above method.
The present invention also provides the method for preparing methionine using above-mentioned Sodium L-methioninate,
Optionally, the saponification liquor obtained enters ion exchange resin system.
Optionally, the ion exchange resin system is selected from cation exchange resin system.
Optionally, the cation exchange resin system is selected from hydrogen type cation exchange resin system.
Optionally, the carbon dioxide and ammonia of discharge are recycled through gas-liquid separator, are back to 5- [2- (methyl mercapto) ethyl]
Glycolylurea synthesis procedure recycles.
The present invention also provides the methionine according to made from the above method.
As described above, the method that 5- [2- (methyl mercapto) ethyl] glycolylurea hydrolysis exhaust of the invention prepares methionine, at least
Have the advantages that (1) present invention reduces 5- [2- (methyl mercapto) ethyl] glycolylurea hydrolysising alkali of Cymag methionine method
It is high to solve the problems, such as that alkali consumes for throwing amount, saves and uses alkali 30wt%, directly reduction methionine production cost.
(2) present invention reduces carbonate contents in saponification liquor, effectively reduce the capacity of ion exchange link, institute
It obtains saponification liquor and is directly entered ion exchange system, while improving the processing capacity of ion exchange resin, be not necessarily to methionine glycolylurea
The aqueous solution containing methionine is added in hydrolyzate to be hydrolyzed again.
(3) present invention effectively reduces the total alkali content in methionine production technology.Thus calculating reduces by-product sodium sulphate,
Save the nearly 30wt% of sulfuric acid.
(4) present invention process method is simple, easily operated, and exploitativeness is strong.
Specific embodiment
Illustrate embodiments of the present invention below by way of specific specific example, those skilled in the art can be by this specification
Other advantages and efficacy of the present invention can be easily understood for disclosed content.The present invention can also pass through in addition different specific realities
The mode of applying is embodied or practiced, the various details in this specification can also based on different viewpoints and application, without departing from
Various modifications or alterations are carried out under spirit of the invention.
It solves the problems, such as that methionine hydrolysising alkali consumes high premise and is not introduce new impurity, does not reduce yield.With
Methacrylaldehyde and methyl mercaptan are that raw material generates methylthiopropionaldehyde, and methylthiopropionaldehyde and the ammonia spirit of Cymag, ammonium bicarbonate are condensed
Reaction generates 5- [2- (methyl mercapto) ethyl] glycolylurea, is then produced in the technique of methionine by basic hydrolysis, ion exchange, for
Wherein using the resulting 5- of condensation reaction [2- (methyl mercapto) ethyl] glycolylurea as raw material, with suitable basic hydrolysis generate methionine salt and
This link of carbonate, one kind has been arrived in present invention exploration can reduce the sea 5- in Cymag methionine method [2- (methyl mercapto) ethyl]
The method of alkali throwing amount when because of hydrolysis.
Embodiment 1
In 1000mL autoclave, 528 Kehaiyin medicine aqueous solutions are added, and (5- [2- (methyl mercapto) ethyl] glycolylurea content is
13.3wt%, sodium ions content 2.15wt%, surplus are water, pH=9.75) and 13.2 grams of solid sodium hydroxides (96wt%).
Then agitating and heating is warming up to 175 DEG C, keeps the temperature 30 minutes, and in the process, it is slow that pressure opens exhaust valve when reaching 1.0MPa
Exhaust keeps certain exhaust, reacts whole pressure control in 0.8MPa or so.After heating, 40 DEG C or so are cooled to, it will
Resulting yellow clarification saponification liquor is poured out, and is weighed 510 grams of saponification liquor, by analysis, wherein Sodium L-methioninate content is
17.49wt%, carbonate content 1.31wt%, are not detected 5- [2- (methyl mercapto) ethyl] glycolylurea, and saponification liquor pH is 10.42.
Embodiment 2
In 1000mL autoclave, 534 Kehaiyin medicine aqueous solutions are added, and (5- [2- (methyl mercapto) ethyl] glycolylurea content is
13.3wt%, sodium ions content 2.15wt%, surplus are water, pH=9.75) and 26.2 grams of 50wt% sodium hydrate aqueous solutions.
Then agitating and heating is warming up to 173 DEG C, keeps the temperature 15 minutes, and in the process, it is slow that pressure opens exhaust valve when reaching 1.0MPa
Exhaust keeps certain exhaust, reacts whole pressure control in 0.8MPa or so.After heating, 40 DEG C or so are cooled to, it will
Resulting yellow clarification saponification liquor is poured out, and is weighed 540 grams of saponification liquor, by analysis, wherein Sodium L-methioninate content is
17.48wt%, carbonate content 1.23wt%, are not detected 5- [2- (methyl mercapto) ethyl] glycolylurea, and saponification liquor pH is 10.45.
Embodiment 3
In 1000mL autoclave, 544 Kehaiyin medicine aqueous solutions are added, and (5- [2- (methyl mercapto) ethyl] glycolylurea content is
13.3wt%, sodium ions content 2.15wt%, pH=9.75) and 26.7 grams of 50wt% sodium hydrate aqueous solutions.Then it stirs
170 DEG C are heated to, keeps the temperature 15 minutes, exhaust valve is opened in the process, when pressure reaches 1.0MPa and is slowly vented, keep
Certain exhaust reacts whole pressure control in 0.8MPa or so.After heating, 40 DEG C or so are cooled to, by resulting soap
Change liquid to pour out, weigh 558 grams of saponification liquor, by analysis, wherein Sodium L-methioninate content is 17.21wt%, and carbonate content is
1.29wt%, is not detected 5- [2- (methyl mercapto) ethyl] glycolylurea, and saponification liquor pH is 10.58.
Embodiment 4
In 1000mL autoclave, 520 Kehaiyin medicine aqueous solutions are added, and (5- [2- (methyl mercapto) ethyl] glycolylurea content is
13.08wt%, sodium ions content 2.10wt%, pH=9.69) and 25.0 grams of 50wt% sodium hydrate aqueous solutions.Then it stirs
170 DEG C are heated to, keeps the temperature 15 minutes, exhaust valve is opened in the process, when pressure reaches 1.0MPa and is slowly vented, keep
Certain exhaust reacts whole pressure control in 0.8MPa or so.After heating, 40 DEG C or so are cooled to, by resulting soap
Change liquid to pour out, weigh 519 grams of saponification liquor, by analysis, wherein Sodium L-methioninate content is 17.09wt%, and carbonate content is
1.03wt%, is not detected 5- [2- (methyl mercapto) ethyl] glycolylurea, and saponification liquor pH is 10.45.
Embodiment 5
In 1000mL autoclave, 512 Kehaiyin medicine aqueous solutions are added, and (5- [2- (methyl mercapto) ethyl] glycolylurea content is
13.20wt%, sodium ions content 2.14wt%, pH=9.8) and 24.8 grams of 50wt% sodium hydrate aqueous solutions.Then it stirs
170 DEG C are heated to, keeps the temperature 15 minutes, exhaust valve is opened in the process, when pressure reaches 1.0MPa and is slowly vented, keep
Certain exhaust reacts whole pressure control in 0.8MPa or so.After heating, 40 DEG C or so are cooled to, by resulting soap
Change liquid to pour out, weigh 520 grams of saponification liquor, by analysis, wherein Sodium L-methioninate content is 16.80wt%, and carbonate content is
1.15wt%, is not detected 5- [2- (methyl mercapto) ethyl] glycolylurea, and saponification liquor pH is 10.45.
Embodiment 6
In 1000mL autoclave, 808 Kehaiyin medicine aqueous solutions are added, and (5- [2- (methyl mercapto) ethyl] glycolylurea content is
12.50wt%, sodium ions content 2.06wt%, pH=9.8) and 37.2 grams of 50wt% sodium hydrate aqueous solutions.Then it stirs
172 DEG C are heated to, keeps the temperature 15 minutes, exhaust valve is opened in the process, when pressure reaches 1.0MPa and is slowly vented, keep
Certain exhaust reacts whole pressure control in 0.8MPa or so.After heating, 40 DEG C or so are cooled to, by resulting soap
Change liquid to pour out, weigh 810 grams of saponification liquor, by analysis, wherein Sodium L-methioninate content is 17.26wt%, and carbonate content is
1.40wt%, is not detected 5- [2- (methyl mercapto) ethyl] glycolylurea, and saponification liquor PH is 10.34.
The resulting saponification liquor of above-described embodiment 1-6 can be directly entered sodium form cation exchange resin system and be handled.
Reference examples 1
In 1000mL autoclave, 547 Kehaiyin medicine aqueous solutions are added, and (5- [2- (methyl mercapto) ethyl] glycolylurea content is
15.97wt%, sodium ions content 2.46wt%, pH=9.71) and 67.0 grams of 50wt% sodium hydrate aqueous solutions.Then it stirs
172 DEG C are heated to, keeps the temperature 15 minutes, whole pressure is reacted and is greater than 1.5MPa.After heating, 40 DEG C or so are cooled to,
Resulting saponification liquor is poured out, is weighed 585 grams of saponification liquor, by analysis, wherein Sodium L-methioninate content is 17.34wt%, carbonic acid
Radical content is 3.01wt%, and 5- [2- (methyl mercapto) ethyl] glycolylurea is not detected, and saponification liquor pH is 10.51.
From above-described embodiment and reference examples can be seen that glycolylurea amount of aqueous solution used close in the case where, hydrogen when not being vented
The dosage of sodium hydrate aqueous solution when the dosage of aqueous solution of sodium oxide is much larger than exhaust, also, when not being vented in gained saponification liquor
Carbonate content much higher than exhaust when gained saponification liquor in carbonate content much higher than exhaust when, carbonate content is higher,
The processing capacity that later period carries out resin when ion-exchange treatment is lower.
In conclusion one aspect of the present invention can reduce the investment of alkali, energy consumption can be reduced on the other hand, it can also be big
Big promotion ion-exchange processing capacity substantially reduces the by-product of sodium sulphate during production methionine, and this method is simple, easily grasps
Make, exploitativeness is strong.
The above-described embodiments merely illustrate the principles and effects of the present invention, and is not intended to limit the present invention.It is any ripe
The personage for knowing this technology all without departing from the spirit and scope of the present invention, carries out modifications and changes to above-described embodiment.Cause
This, institute is complete without departing from the spirit and technical ideas disclosed in the present invention by those of ordinary skill in the art such as
At all equivalent modifications or change, should be covered by the claims of the present invention.
Claims (10)
1. a kind of method that 5- (2- methyl mercapto)-hydantoins hydrolysis exhaust prepares Sodium L-methioninate characterized by comprising will
Aqueous solution of the glycolylurea aqueous solution with alkali or containing alkali mixes；Resulting mixed liquor is heated to 140 DEG C of -190 DEG C of reactions, reaction process
In be exhausted, obtain the saponification liquor containing Sodium L-methioninate.
2. according to the method described in claim 1, it is characterized by: it is described reaction be to be carried out in closed container, pass through exhaust
Maintain the pressure in the closed container, pressure >=0.7MPa in the closed container, preferably 0.7-1.1MPa.
3. according to the method described in claim 1, it is characterized by: 5- [2- (methyl mercapto) ethyl] is extra large in the glycolylurea aqueous solution
Because content is 10wt%-20wt%；
And/or the glycolylurea Na in Solution ion concentration is 1.6wt%-2.6wt%；
And/or the glycolylurea aqueous solution is the aqueous solution containing 5- [2- (methyl mercapto) ethyl] glycolylurea and sodium carbonate.
4. according to the method described in claim 1, it is characterized by: the alkali and 5- [2- (methyl mercapto) second in glycolylurea aqueous solution
Base] glycolylurea molar ratio be (0.6-1): 1；
And/or the alkali is selected from least one of sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate.
5. according to the method described in claim 1, it is characterized by: the mass fraction of alkali is in the aqueous solution containing alkali
40wt%-55wt%.
6. according to the method described in claim 1, it is characterized by: carbonate content in the obtained saponification liquor≤
1.5wt%.
7. Sodium L-methioninate made from -6 any one the methods according to claim 1.
8. the method for preparing methionine using Sodium L-methioninate described in claim 7, it is characterised in that: the obtained saponification liquor into
Enter ion exchange resin system, it is preferable that the ion exchange resin system is selected from cation exchange resin system, more preferably
Ground, the cation exchange resin system are selected from hydrogen type cation exchange resin system.
9. according to the method described in claim 8, returning it is characterized by: carbon dioxide and ammonia to discharge recycle
It is recycled to 5- [2- (methyl mercapto) ethyl] glycolylurea synthesis procedure.
10. methionine made from method according to claim 8 or claim 9.
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| CN201910652656.4A CN110305050A (en) | 2019-07-18 | 2019-07-18 | A kind of method that 5- [2- (methyl mercapto) ethyl] glycolylurea hydrolysis exhaust prepares Sodium L-methioninate |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1092158A (en) * | 1964-12-29 | 1967-11-22 | Sumitomo Chemical Co | Process for producing alpha-amino acids |
| CN85108531A (en) * | 1985-11-14 | 1987-05-20 | 西北大学 | The method of 5-(β-methylmercaptoethyl) glycolylurea preparation of methionine by hydrolyzing |
| CN1376671A (en) * | 1995-12-18 | 2002-10-30 | 底古萨股份公司 | Method for preparing methylthioamino acid or alkali salts thereof |
| CN104910055A (en) * | 2015-06-30 | 2015-09-16 | 西安蓝晓科技新材料股份有限公司 | Method for extracting methionine |
-
2019
- 2019-07-18 CN CN201910652656.4A patent/CN110305050A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1092158A (en) * | 1964-12-29 | 1967-11-22 | Sumitomo Chemical Co | Process for producing alpha-amino acids |
| CN85108531A (en) * | 1985-11-14 | 1987-05-20 | 西北大学 | The method of 5-(β-methylmercaptoethyl) glycolylurea preparation of methionine by hydrolyzing |
| CN1376671A (en) * | 1995-12-18 | 2002-10-30 | 底古萨股份公司 | Method for preparing methylthioamino acid or alkali salts thereof |
| CN104910055A (en) * | 2015-06-30 | 2015-09-16 | 西安蓝晓科技新材料股份有限公司 | Method for extracting methionine |
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